1-(2,3-Dideoxy-5-O - tert-butyldiphenylsilyl-alpha, beta-L-ribofuranosyl)-cytosine

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1-(2,3-Dideoxy-5-O - tert-butyldiphenylsilyl-alpha, beta-L-ribofuranosyl)-cytosine
• 英文别名: 4-amino-1-[(5R)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]oxolan-2-yl]pyrimidin-2-one
• 化学式: C₂₅H₃₁N₃O₃Si
• 分子量: 449.625
• InChiKey: KOTSFFBBGPFTAA-HWYAHNCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.08
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  77.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2,3-Dideoxy-5-O - tert-butyldiphenylsilyl-alpha, beta-L-ribofuranosyl)-cytosine 在 四乙基氟化铵水合物 作用下， 以 四氢呋喃 为溶剂， 生成 2(1H)-嘧啶酮,4-氨基-1-[(2S,5R)-四氢-5-(羟甲基)-2-呋喃基]- 、 1-(α-L-2',3'-dideoxyribofuranosyl)cytosine
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Pyrimidine and Purine α-L-2′,3′-Dideoxy Nucleosides

  摘要：

  A series of alpha-L-2',3'-dideoxy nucleosides was prepared as potential antiviral agents. The pyrimidine nucleosides were prepared by standard Vorbruggen coupling reactions. The purine analogues were prepared by enzymatic transfer of the dideoxy sugar from a pyrimidine to a purine base. These compounds were inactive against HIV-1, HBV, HSV-I and -2, VZV, and HCMV.

  DOI：

  10.1080/15257779408009473
• 作为产物：
  描述：

  胞嘧啶 、 (4R)-1-O-acetyl-5-O-tert-butyldiphenylsilyl-2,3-dideoxy-L-ribofuranose 在 N,O-双三甲硅基乙酰胺 、 三氟甲磺酸三甲基硅酯 作用下， 以 甲苯 、 乙腈 为溶剂， 生成 1-(2,3-Dideoxy-5-O - tert-butyldiphenylsilyl-alpha, beta-L-ribofuranosyl)-cytosine
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Pyrimidine and Purine α-L-2′,3′-Dideoxy Nucleosides

  摘要：

  A series of alpha-L-2',3'-dideoxy nucleosides was prepared as potential antiviral agents. The pyrimidine nucleosides were prepared by standard Vorbruggen coupling reactions. The purine analogues were prepared by enzymatic transfer of the dideoxy sugar from a pyrimidine to a purine base. These compounds were inactive against HIV-1, HBV, HSV-I and -2, VZV, and HCMV.

  DOI：

  10.1080/15257779408009473

文献信息

• Synthesis and Biological Evaluation of Pyrimidine and Purine α-L-2′,3′-Dideoxy Nucleosides
  作者：Naina A. Van Draanen、George W. Koszalka

  DOI：10.1080/15257779408009473

  日期：1994.9

  A series of alpha-L-2',3'-dideoxy nucleosides was prepared as potential antiviral agents. The pyrimidine nucleosides were prepared by standard Vorbruggen coupling reactions. The purine analogues were prepared by enzymatic transfer of the dideoxy sugar from a pyrimidine to a purine base. These compounds were inactive against HIV-1, HBV, HSV-I and -2, VZV, and HCMV.